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NMR Spectroscopy: Spin–Spin Coupling

NMR Spectroscopy: Spin–Spin Coupling

The spin state of an NMR-active nucleus can have a slight effect on its immediate electronic environment. This effect propagates through the intervening bonds and affects the electronic environments of NMR-active nuclei up to three bonds away; occasionally, even farther. This phenomenon is called spin–spin coupling or J-coupling. Coupling interactions are mutual and result in small changes in the absorption frequencies of both nuclei involved. While nuclei of the same element are involved in...

Spin–Spin Coupling Constant: Overview

Spin–Spin Coupling Constant: Overview

In bromoethane, the three methyl protons are coupled to the two methylene protons that are three bonds away. In accordance with the n+1 rule, the signal from the methyl protons is split into three peaks with 1:2:1 relative intensities. The methylene protons appear as a quartet, with the relative intensities of 1:3:3:1.
Qualitatively, any spin plus-half nucleus polarizes the spins of its electrons to the minus-half state. Consequently, the paired electron in the hydrogen–carbon bond must have a...

Spin–Spin Coupling: One-Bond Coupling

Spin–Spin Coupling: One-Bond Coupling

Coupling interactions are strongest between NMR-active nuclei bonded to each other, where spin information can be transmitted directly through the pair of bonding electrons. While nuclei polarize their electrons to the opposite spins, the bonding electron pair has opposite spins. Configurations with antiparallel nuclear spins are expected to be lower in energy. When coupling makes antiparallel states more favorable, J is considered to have a positive value. The one-bond coupling constant, 1J,...

Spin–Spin Coupling: Two-Bond Coupling (Geminal Coupling)

Spin–Spin Coupling: Two-Bond Coupling (Geminal Coupling)

Two NMR-active nuclei bonded to a central atom can be involved in geminal or two-bond coupling. Geminal coupling is commonly seen between diastereotopic protons in chiral molecules and unsymmetrical alkenes, among others.
The central atom need not be NMR-active because its electrons are affected by the electron polarization of the spin-active atoms. However, spin information is transmitted less effectively than in one-bond coupling, and 2J values are usually weaker than 1J values. The energy of...

Spin–Spin Coupling: Three-Bond Coupling (Vicinal Coupling)

Spin–Spin Coupling: Three-Bond Coupling (Vicinal Coupling)

Vicinal or three-bond coupling is commonly observed between protons attached to adjacent carbons. Here, nuclear spin information is primarily transferred via electron spin interactions between adjacent C‑H bond orbitals. This generally favors the antiparallel arrangement of spins, so 3J values are usually positive.
The extent of coupling depends on the C‑C bond length, the two H‑C‑C angles, any electron-withdrawing substituents, and the dihedral angle between the involved orbitals. The...

¹H NMR: Long-Range Coupling

¹H NMR: Long-Range Coupling

The coupling interactions of nuclei across four or more bonds are usually weak, with J values less than 1 Hz. While these are usually not observed in spectra, the presence of multiple bonds along the coupling pathway can result in observable long-range coupling.
In alkenes, spin information is communicated via σ–π overlap, as seen in allylic (four-bond) and homoallylic (five-bond) couplings. These coupling interactions are stronger when the σ bond is parallel to the alkene π orbitals.

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An unusual seven-bond H-H spin coupling

Bhacca¹, Juneau, Lankin

¹Department of Chemistry, Louisiana State University, Baton Rouge, Louisiana 70803, USA.

Organic Letters

|December 2, 2000

Summary

A seven-bond (1)H-(1)H coupling was observed in tiliacorinine due to close proximity of aromatic protons. This unusual spatial arrangement was confirmed using advanced Nuclear Magnetic Resonance (NMR) techniques and molecular modeling.

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Area of Science:

Organic Chemistry
Structural Elucidation
Nuclear Magnetic Resonance Spectroscopy

Background:

Tiliacorinine is a complex natural product with potential biological activities.
Understanding the three-dimensional structure of such molecules is crucial for structure-activity relationship studies.
Through-space couplings in Nuclear Magnetic Resonance (NMR) spectroscopy can provide unique structural insights.

Purpose of the Study:

To investigate the observed seven-bond (1)H-(1)H coupling in tiliacorinine.
To elucidate the structural basis for this through-space coupling.
To confirm the close spatial proximity of specific aromatic protons in tiliacorinine.

Main Methods:

Detailed Nuclear Magnetic Resonance (NMR) experiments, including Double Quantum Filtered Correlation Spectroscopy (DQF-COSY) and Nuclear Overhauser Effect Spectroscopy (NOESY).
Molecular modeling studies to assess spatial arrangements of atoms and protons.
Analysis of through-space, seven-bond (1)H-(1)H coupling constants.

Main Results:

A through-space, seven-bond (1)H-(1)H coupling was successfully observed and characterized in tiliacorinine.
The coupling arises from two aromatic protons in different benzene rings, separated by two sp(3) carbons.
Results indicate an unusually close spatial proximity between these two protons, consistent across NMR data and modeling.

Conclusions:

The study confirms a rare seven-bond through-space (1)H-(1)H coupling in tiliacorinine.
This finding highlights the utility of advanced NMR techniques and molecular modeling for detailed structural analysis.
The close spatial arrangement provides valuable information for understanding tiliacorinine's conformation and properties.